Calendar Booking Debugging Guide

Background & Purpose

This SOP is designed to assist in troubleshooting issues related to conversational calendar booking for client-facing interactions. Following the outlined CASPER triage process ensures efficient problem identification and resolution, enabling the booking bot to perform as intended and provide reliable support for AI deployment.

Required Resources

• Access to conversational booking tool (e.g., GoHighLevel)
• Logs for tool activity (availability checks and booking actions)
• Client’s calendar settings and availability link
• Access to assistant configuration (e.g., prompts, calendar connections)

The CASPER Methodology

Use this systematic triage order: C-A-S-P-E-R

C - Calendar Access

A - Ability (Tools)

S - Settings

P - Prompt

E - Event Tool Calls

R - Refresh Connection

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1. Calendar Access (C)

Objective

Ensure the assistant has access to the specific calendar and verify correct integration.

Verification Steps

Check Calendar Integration

1. Navigate to Assistant Settings
2. Go to the Calendars tab
3. Verify calendar is listed and connected

Add Calendar if Missing

1. Click “Add Calendars” to open the calendar menu
2. Sync your calendars with GoHighLevel
3. Click “Add to Assistant” to begin verification process

Verification Process

• The verification process runs a simulation for booking
• Calendar only verifies if simulation is successful
• Look for green checkmark in upper right corner after verification
• Click “Add to Assistant” to complete the process

Success Criteria

✅ Calendar appears in assistant’s calendar list ✅ Green checkmark indicates successful verification ✅ Calendar is actively connected to assistant

Troubleshooting

Calendar not appearing:

• Check GoHighLevel calendar permissions
• Verify calendar is properly configured in GoHighLevel
• Ensure OAuth connection is active

Verification failing:

• Review calendar availability settings
• Check for booking conflicts or restrictions
• Verify calendar has available time slots

2. Ability (A)

Objective

Confirm the assistant has access to essential tool calls for calendar management.

Required Tools for Booking

• Check Availability - Retrieves available time slots
• Book Appointment - Creates appointments on calendar

Verification Steps

Check Existing Tools

1. Navigate to Tools & Abilities in assistant settings
2. Verify presence of calendar management tools
3. Confirm “Check Availability” and “Book Appointment” are enabled

Add Missing Tools

1. Click “Add Function” if tools are missing
2. Select from pre-built tools (should be first two options)
3. Enable required calendar tools

Additional Useful Tools

• Reschedule Appointments - Modify existing bookings
• Cancel Appointments - Remove scheduled appointments
• Check Contact’s Current Appointments - View existing bookings

Success Criteria

✅ “Check Availability” tool is enabled ✅ “Book Appointment” tool is enabled ✅ Tools appear in assistant’s function list

Troubleshooting

Tools not working:

• Verify tool permissions are correctly set
• Check tool configuration parameters
• Test tools with simple booking scenarios

3. Settings (S)

Objective

Verify calendar settings to ensure booking works as expected and availability is correctly configured.

Calendar Settings Verification

Access Calendar Settings

1. Navigate to Calendars in GoHighLevel
2. Go to Calendar Settings
3. View all configured calendars

Check Objective Availability

1. Click the 3 dots on your calendar
2. Click “Share” to open popup
3. Copy the permanent calendar link
4. Paste link in new tab to view public availability

Common Settings Issues

Third-Party Calendar Integration

Problem: Google or other calendar integration blocking availability Solution:

• Review third-party calendar settings
• Check for personal calendar conflicts
• Adjust integration settings to allow availability

General Calendar Settings

Potential Conflicts:

• “Look Busy” settings limiting availability
• Date range restrictions blocking certain periods
• Buffer time conflicts consuming available slots
• Working hours not properly configured

Settings Audit Checklist

• ✅ Working hours align with intended availability
• ✅ Buffer times are appropriate
• ✅ Third-party integrations don’t block availability
• ✅ Date restrictions are properly configured
• ✅ Public availability matches expectations

Troubleshooting

Availability doesn’t match expectations:

• Review all calendar integrations
• Check working hours and time zones
• Verify buffer and break settings
• Audit any special restrictions or rules

4. Prompt (P)

Objective

Ensure prompts are concise and focused solely on booking tasks without confusion.

The Simplicity Principle

Key Insight: You can create a perfectly functional booking assistant with a simple prompt: “You are an appointment booking bot”

Common Prompt Problems

Information Overload

Problem: Using prompt as a place to dump context and information Issues:

• Confuses the AI about primary objectives
• Creates conflicting instructions
• Interferes with booking functionality

Solution: Use appropriate tools for different content types:

Proper Content Distribution

Prompt Should Contain:

• Personality/Identity - Who the assistant is
• Response Guidelines - How to communicate
• Style Guardrails - Tone and approach
• Important Points - Key behavioral notes
• Instruction Set - What to do and when

Knowledge Base Should Contain:

• Domain Knowledge - Industry-specific information
• Business Information - Company details
• FAQs - Frequently asked questions
• Objection Handling - Response strategies
• Pricing Information - Simple pricing details
• Key-Value Trained Output - Structured responses

Tools Should Handle:

• Context Injection - Conditional instructions
• Data Retrieval - Getting information
• Data Processing - Performing actions
• Parameter Scaling - Dynamic functionality

Prompt Best Practices

Structure Guidelines

• Be concise and direct
• Use clear, simple language
• Avoid complex scenario handling
• Remove unnecessary markdown (only use ## headers)
• Focus on core booking functionality

Example Effective Booking Instruction

6. Get your availability and use that to book an appointment with the user

Success Criteria

✅ Prompt is concise and focused ✅ Booking instructions are clear and simple ✅ No conflicting or confusing directives ✅ Business information moved to knowledge base

Troubleshooting

AI not following booking protocol:

• Simplify prompt language
• Remove conflicting instructions
• Separate business info into knowledge base
• Test with minimal prompt first

5. Event Tool Calls (E)

Objective

Confirm tools successfully execute for booking and availability checking.

Log Analysis

Check Task Performed Events

1. Review conversation logs
2. Look for “Task Performed” entries
3. Examine metadata for tool calls

Availability Check Issues

AI Giving Improper Times:

• Verify availability tool call shows in logs
• Check metadata for retrieved time slots
• Compare with actual GoHighLevel availability
• If discrepancy exists: Review calendar settings (not OAuth issue)

Common Prompt Conflicts:

• Conflicting booking instructions
• Unclear language around appointment scheduling
• Complex time handling instructions

Booking Execution Issues

AI Giving Correct Times but Not Booking:

• Check booking tool metadata for GoHighLevel response
• Review error codes in tool call results

Common Error Scenarios:

• Authorization Errors: OAuth configuration issues
• Bad Request: Instruction injection or timezone conflicts
• Permission Denied: Insufficient OAuth permissions

Tool Call Verification

Successful Tool Calls Should Show:

• Timestamps for when tools were executed
• Calendar details in metadata
• Response metadata (e.g., “appointment booked”)
• No error codes like “unauthorized” or “bad request”

Success Criteria

✅ Availability checks show correct time slots ✅ Booking attempts execute successfully ✅ Tool metadata shows proper responses ✅ No authorization or permission errors

Troubleshooting

Tool calls failing:

• Check OAuth connection status
• Verify tool permissions
• Review instruction clarity
• Test with simple booking scenarios

6. Refresh Connection (R)

Objective

If all settings and tools appear correctly configured but issues persist, refresh all connections.

Comprehensive Refresh Process

OAuth Connection Reset

1. Disconnect OAuth from GoHighLevel
2. Clear any cached connections
3. Reconnect with fresh authentication
4. Verify all permissions are granted

Tool Refresh

1. Remove calendar tools from assistant
2. Re-add tools with fresh configuration
3. Test each tool individually
4. Verify tool permissions

Calendar Resync

1. Delete calendar from assistant
2. Resync calendar with GoHighLevel
3. Complete verification process again
4. Test booking functionality

Prompt Reset

1. Simplify prompt to basics
2. Remove unnecessary information
3. Build complexity gradually
4. Test after each modification

Testing After Refresh

1. Run simple availability check
2. Attempt test booking
3. Verify booking appears in calendar
4. Test with multiple time slots

Success Criteria

✅ Fresh OAuth connection established ✅ Tools responding correctly ✅ Calendar properly synced ✅ Test bookings work flawlessly

Definition of Done

This debugging checklist is complete when:

• ✅ Assistant accurately checks for availability
• ✅ Booking functionality works reliably
• ✅ Calendar times align with intended availability
• ✅ Prompts are clean and focused
• ✅ Tool call logs show successful operations
• ✅ No error responses in system logs

Additional Troubleshooting

Common Error Messages

”Unauthorized” Error

Cause: OAuth connection issues Solution:

• Refresh OAuth connection
• Verify all permissions granted
• Check GoHighLevel account access

”Bad Request” Error

Cause: Instruction injection or data formatting issues Solution:

• Simplify booking instructions
• Let AI handle timezone conversions naturally
• Remove conflicting prompt directives

Incorrect Availability Times

Cause: Calendar configuration issues Solution:

• Check GoHighLevel calendar settings
• Review third-party calendar integrations
• Verify working hours and restrictions

Quick Reference CASPER Checklist

C - Calendar Access

• Calendar connected to assistant
• Verification successful (green checkmark)
• Calendar appears in assistant settings

A - Ability (Tools)

• “Check Availability” tool enabled
• “Book Appointment” tool enabled
• Tools configured with proper permissions

S - Settings

• Calendar availability matches expectations
• Third-party integrations working correctly
• Working hours and restrictions properly set

P - Prompt

• Prompt is concise and focused
• No conflicting instructions
• Business info moved to knowledge base

E - Event Tool Calls

• Availability checks working in logs
• Booking tool calls successful
• No error codes in metadata

R - Refresh

• OAuth connection refreshed if needed
• Tools removed and re-added
• Calendar resynced if necessary

Best Practices

Prompt Engineering

• Start simple with basic booking instructions
• Add complexity gradually only when needed
• Test each change thoroughly
• Keep business information in knowledge base

System Maintenance

• Regular OAuth checks to ensure connection health
• Periodic calendar setting audits
• Monitor tool call success rates
• Keep prompts clean and focused

Testing Strategy

• Test with real scenarios regularly
• Use multiple time slots for testing
• Verify bookings appear correctly in calendar
• Check from user perspective using public calendar link

This comprehensive debugging guide ensures reliable calendar booking functionality through systematic troubleshooting and best practices implementation.